


A Moment Changes Everything

by Hells_Brat



Category: Supernatural
Genre: ALL THE FIRSTS, Alternate Universe, Alternate Universe - College/University, Alternate Universe - High School, Alternate Universe - Modern Setting, Alternate Universe- No Supernatural, Childhood Friends, Childhood Sweethearts, Dean fucks up, Dialogue Heavy, Discussion of Abortion, Domestic Fluff, F/M, Falling In Love, Fluff, Fluff and Angst, Forgiveness, Growing Up Together, Guilt, Heartbreak, Implied/Referenced Abortion, Implied/Referenced Cheating, Implied/Referenced Underage Drinking, Implied/Referenced Underage Sex, Jealousy, John Winchester & Mary Winchester Live, Lisa Braeden Bashing, Lisa Braeden Being an Asshole, Minor Castiel/Meg Masters, Minor Jessica Moore/Sam Winchester, Minor Lisa Braeden/Dean Winchester, Past Lisa Braeden/Dean Winchester, Possible Humor (I hope I'm as funny as I think I am), Protective Dean Winchester, Reader-Insert, Reader-Interactive, Teen Dean Winchester, Teen Sam Winchester, Teenage Rebellion, Underage Drinking, Underage Sex, Unplanned Pregnancy, Young Dean Winchester, Young Sam Winchester
Language: English
Status: In-Progress
Published: 2019-12-30
Updated: 2020-11-25
Packaged: 2021-02-26 02:21:17
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply, Underage
Chapters: 5
Words: 9,789
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21725929
Author URL: https://archiveofourown.org/users/Hells_Brat/pseuds/Hells_Brat
Summary: Every relationship has it's ups and downs, but for the most part, life with Dean was damn near sitcom style awesome, only with much more swearing. Until one drunken mistake ruined everything.A series of non-linear snapshots of your life with Dean, through the years and how you had to live without him before you were able to forgive him.
Relationships: Dean Winchester/Reader, Dean Winchester/You
Comments: 11
Kudos: 33





	1. I Wish I Never Saw the Sunshine

**Notes for the Chapter:**

> All of my dreams, I dreamed with you  
> Now they will die and never come true  
> And I keep crying
> 
> [The Ronettes - I Wish I Never Saw the Sunshine (the original)](https://www.youtube.com/watch?v=1ZovCE4byCY)  
> or  
> [Beth Orton - I Wish I Never Saw the Sunshine (my favorite)](https://www.youtube.com/watch?v=XR2gaDtS1js)

It was never supposed to end like this. Hell, it wasn't supposed to end in the first place, but here you were back in your childhood home for the unforeseeable future. You suppose you could have thrown Dean out of the apartment, but after everything you couldn't stay there a moment longer. Not when it was devoid of the all laughter and love that once filled it's walls, making it a home.

 _'How could I have been so naive? So trusting? And when did I become so fucking stupid,'_ you chided yourself for what had to be the millionth time as you sat on the floor of your childhood bedroom. 

With a scream that began in a broken place from deep within, and ripped through your throat, only to leave a burning pain in its wake, you knocked over the box you were supposed to be unpacking, its contents spilling onto the floor before the overwhelming feeling of loss had you curling up into a sobbing ball on the blush colored carpeting. 

Half a dozen unopened boxes surrounded you, like a castle wall, but that wall did little to protect you because oh so long ago, you threw open the gates and welcomed a green-eyed traitor into your kingdom with open arms. 

That green-eyed traitor wasn't always the enemy. Once, he had been the boy that sat on the porch and shared his cookies with you, the boy who would take your hand to be sure you'd follow. He built made up snow creatures with you in the winter and played on the swing set in your backyard, late into the night, during the summer. 

As time went on, the boy grew into a charismatic young man, who had all the right words, not just for you, but for all the girls who crossed his path. It was much to their dismay, even after some other girl had caught his eye, he always made sure there was time for you. 

How were you to have known that one day, that green eyed man, who told you he loved you a million times, would, in one selfish moment, tear down the world with a single, silent admission? 

Those brown boxes that were abandon at the grocery store had been cluttering up the room for weeks, but unpacking them was simply too difficult. There was a sense of finality in unpacking. Unpacking meant you were staying, that it really was over and you kept telling yourself that this living situation was only temporary, but the real reason behind your procrastination was that you were tired. 

All the energy had been vacuumed out of you, and what little you managed to muster was reserved for getting out of bed in the morning. Anything beyond that, like eating, breathing or even the simple act of trying to exist like an actual human was a true blue miracle, and you weren't quite sure how you hadn't been fired yet. 

On the more difficult mornings, it took a great amount of effort not to ask your mother to call into work sick for you or more appropriately to call you in dead. Dead seemed much more fitting since the future you and Dean had been working toward had been callously stolen and you couldn't see a point in anything anymore. And there was a big future in the works, too. It was only a matter of time before living together turned into a trip down the aisle, and after that, it would be starting a family of your own, something he always wanted. 

In fact, he may have wanted to start a family even more than you did. You wanted to be finished with school, and work for a few years before you even thought about having kids, but he wanted it all tomorrow. Once his father had started giving him more responsibility at the garage, in preparation for his slow journey into retirement, he agreed that waiting would be best. You couldn't help but wonder if maybe it was fortuitous to want to wait, or else you'd be a single mom, dragging an innocent child through a bad break up. 

And bad this break up was. He had left you completely unprepared for the end. How were you to have seen it coming when he had promised forever, and foolishly you believed all of his pretty words. Perhaps that was why his betrayal hurt worse than any pain you'd suffered. If only he had shown you a sign, given you any reason to doubt his love, his words, his promises, even for a moment, maybe then the blow wouldn't have felt like your heart had been carved out of your chest with a spoon by the only person you'd ever loved. 

It wasn't that moving back to fifty-five Barker Avenue lessened the pain in your chest, even a little bit, but you had only yourself to blame for that. For being a cliché and falling for the fucking boy next door. The most difficult part had to be that it really didn’t matter where you went in Lawrence, there were always ghosts to be found. 

Barker Avenue, the street you grew up on, held far too many memories of you and him. It was where you shared your first kiss and your twelfth, and most likely your twentieth. You couldn't even get yourself an ice cream cone because The Dairy Queen over on Iowa*, had been your first real adolescent adventure and the first place you both went together, in an act of rebellion, long before either of your parents would ever have allowed it. 

Of course, no movie theater or dive bar was safe, and practically the entire area in and around KU had ghosts of relationship's past roaming around freely. There were several spots that you had to drive by on your way to and from work where Baby's backseat had gotten one hell of a workout. It seemed no matter where you went or what you did, there were ghosts ready to remind you of what you had, and what you lost.

_Fuck!_

Everyone who ever thought this relationship would never go the distance had been proven right, and oh, how you hated proving them right. 

Wait. 

No. 

You might have been the one that packed up your things and ran all the way home, but it wasn't you that did anything wrong. That was Dean. This unhappy meal belonged to him, and it served him right to be alone in an apartment he hated, filled with all the memories that were made there. 

But he didn't care anymore, did he? If he did, he never would have cheated. 

The sound of a car pulling into the driveway, soon, interrupted your thoughts and your heart took a swan dive into the acidic pit of your stomach. Dragging yourself off the floor, you paused in worry before deciding to pull back the curtain. 

It was the window you'd been avoiding with curtains permanently drawn since you moved back. It was the window that was directly across from _his_ old bedroom, and you were relieved to see it was only your parents and his, returning from Sunday brunch. It really sucked that your parents were not only neighbors, they were friends. 

Taking a seat on the bed, you leaned over, reaching for the middle drawer of your nightstand. With a wry chuckle, you found yourself shaking your head in disbelief. After not living there since college, the plastic Fisher Price walkie talkie was right where it had always been. 

Instantly, you began to rearrange the to do list in your head. The Number One spot just went to decluttering your parents house of anything that reminded you of the past. 

**Notes for the Chapter:**

> *Iowa is a street near Barker Avenue in Lawrence, KS, where there happens to be a Dairy Queen. I did far too much research into minutia because my anal retentiveness goes up to 11.


	2. Tonight, Tonight

**Notes for the Chapter:**

> The indescribable moments of your life, tonight  
> The impossible is possible, tonight  
> Believe in me as I believe in you, tonight.
> 
> [Smashing Pumpkins - Tonight, Tonight](https://www.youtube.com/watch?v=NOG3eus4ZSo)  
> 

Back in 1996

"Just take me home." 

Slamming the door of the white Suzuki Samurai, you slouched down in the passenger seat and waited for Cole to make his way to the driver's side. It might have been spring, but it was about to get chilly all up in the wannabe SUV, and the shattered windshield wasn't the only reason. 

Six months. That seemed like a good enough run, or, depending on which friend decided to weigh in, it was six months too long. Either way, it was what it was, and it was about to be over. It wasn't as if you'd been on the prowl for a boyfriend, but when Jo put her matchmaker mind to something she got results, and the result for you was Cole Trenton. He was cute, had his own car and was the kind of guy parents liked, and yours kind of did, except for the car part. 

As first boyfriends go, Cole was fine, nice, but there was something about him that bugged you, something you never could quite put your finger on, at least, not until the incident with Meg, when his true colors came through, and you didn't much care for the shades you were seeing. 

Once it was over, at least Meg would still be on your side. She always hated Cole, and never pretended otherwise, which was why you were where you were. Meg was the sister you'd trade your own in for, without a second thought. She'd been your ride or die since the seventh grade, and, though, you were nowhere close to being the bad ass she was, no one disrespected her in your presence and got away with it. Not even your soon to be ex, not even if she did throw the bottle that cracked his windshield.

The second after Cole put the key in the ignition, he continued his tirade over Meg's latest drunk and disorderly. 

"She was _drunk_ ," you interrupted him after a few minutes, a distinct lack of emotion your voice. It was pretty much known to everyone that Meg could be problematic after having one too many. Most of the time Meg only became volatile if someone dared fuck with her friends. It was that kind of loyalty that made her a great friend. "Anyway, it was kinda your fault. If you didn't lose your shit in front of everyone…"

"So I was supposed to do, what? Sit there and smile while my girlfriend was all over some other dude ?"

You turned in the seat to face him, disbelief in tone, “No. No. No. I wasn't all over _some_ dude. It was Cas." It was utter madness for anyone to even suggest that you had anything beyond platonic intentions for the guy.

With his eyes still on the road, Cole squinted and tilted his head, making his 'really, dude?' face and said, “You were practically dry humping him in front of everyone. That dork's dick saw more action from you tonight than I've seen in months. I guess it's good to know that you can act like a slut when you want."

Though, you should've probably punched him for the slut comment, Meg had done more than enough after he said similar in front of an audience. Besides, if you were being honest - you hadn't exactly shown much interest in his junk for quite some time. 

"Whatever."

"You were _on_ his lap. Giggling and whispering. What the hell would you call that? "

"Uhhhh. Sitting? It was Cas," you emphasized, "It didn't mean anything. Besides, I'm pretty sure he's had a crush on Meg for, like, ever."

At the mention of her name, the conversation shifted into reverse, back to the monotonous topic of his busted windshield. 

The rest of the ride was uncomfortably quiet inside the Suzuki, with the exception of you messing with the radio, changing stations whenever he showed interest in a song. 

It wasn't until Cole pulled into your driveway he spoke, breaking the silence. "Are, uh, your parents still out of town?" 

Sitting up straight, you looked him dead in the eye, "Really? Really, dude? Talk about not reading the room." 

He looked at you, confused. "What?"

Gearing up for the talk, you said, "Right... okay. First you accused me of being a slut, then you fought with my best friend in front of, like, the entire school. That kind of shit won't get you invited An.Nee.Where."

"Your bitch friend busted my windshield." 

"She was drunk and you were being a monumental dick," you said, and started to get out of the car, "We're done. You can come by this week and get your stuff." 

"Are you... Are you dumping me," when the words registered with him, Cole unbuckled his seat belt and angrily got out of the car, storming over to the passenger's side, "Get back in the car, Y/N!" 

Before you could get very far, his fingers roughly dug into your arm, pulling you back toward the car. 

“What the... Get offa me,” you yelled, writhing in his vice-like grip. 

"You don't get to dump me and just walk away!" 

"I got nothing else to say," you spat back as you continued to struggle, "LET.GO!"

Back and forth the yelling went, turning on more than a few porch lights on your street. The noise caught the attention of one house in particular, and a moment later, the front door of 53 Barker Avenue swung open.

Into the night stepped your oldest friend clad in old sweat pants, and the tee of some band he wasn't old enough to have seen in concert. “Hey, Y/N, you trying to wake up the whole neighborhood or what?”

Upon Dean's appearance, Cole froze, still holding you. The tough guy veneer was slowly slipping away, still, he growled against the side of your face, "Get. Back. In. The. Car!"

“It doesn't look like she wants to go anywhere with you,” Dean said, as he lazily made his way down the steps. Everything about him was too calm, which, if history told you anything inside he was pissed.

Quickly, you tried to diffuse any impending situation that might be coming. “Dean, Dee, it’s okay. Cole was just leaving.”

“Yeah, _Dee_ ," Cole said, his tone mocking yours, "I was just leaving. Right after we finish our conversation.”

Dean nodded, his eyes travelling from your face to Cole's grip on your arm, then up to his face, staring with hard eyes. “Come on, dude, it’s late, and it's clear she doesn't want to talk you right now. How about you head on home and you two can work all this out in the morning?”

Returning the stare, Cole said, “How about you fuck off, Winchester?" 

The stare down, along with Dean's slow walk toward you, distracted Cole enough to give you a moment to twist in his grip, before biting down on his arm until you tasted copper on your tongue. 

"Bitch! You fucking bit me," Cole thrashed his arm around, hand releasing you and sending you stumbling in Dean's direction. 

Using his quick reflexes, Dean caught you before you could crash land onto the driveway. While still holding you in his arms, he shot you a wink, and his smug as hell grin, before setting you on your feet. 

For his next trick, he responded to Cole with a right cross to the jaw. The punch was simple, and straight to the point with enough power behind it to knock your ex to the uneven pavement and your brain teetered between shock and amusement, unable (or were you unwilling?) to prevent the single, dry 'ha' from leaving your throat. 

"What the hell, man," Cole groaned from the concrete.

"Shoulda just went home," Dean said, as he flexed his right hand, checking for damage. 

From your peripheral you saw movement from the ground as Cole made a slow, shaky rise to feet. Though it was unlikely he would retaliate, you moved between the two as if to say - side chosen. 

The injured and newly single, Cole made his way to his car, grumbling, "You like the frigid bitch so much you can have her." 

Ignoring Cole's comment, you kept your focus on Dean's hand, "You should probably go put some ice on it."

Shrugging it off, he looked up at you with a crooked, little grin. "It's not that bad." 

"So... how was your game?”

"Really," surprise covered his face, "Since when do you care about baseball?" 

He was right. you didn't care about baseball, you asked because you thoroughly enjoyed his wildly dramatic reenactments, and the enthusiasm that he displayed over things he truly enjoyed. He put his whole body into a story. Wide green eyes lighting up at the highs, and darken at the lows. His face morphed from disappointment to joy with arms that flailed as the excitement grew. It was a ride that never disappointed.

"Come on. Tell me," you whined, needing to take the ride after the night you had. 

Moving closer, he rubbed the back of his neck as he crossed onto your side of the property line. He was wary at first, “Okay, so it didn't start off real good..." 

You nodded as he spoke, and threw in an occasional sound to show interest, but as he got going, the action began to animate him,"*We were down 2-1 until Garth, you know Garth Fitzgerald, he hit a double in the seventh then Kevin Tran followed, tying the game. Two outs later, the super handsome and all around awesome guy, yours truly, got up to the plate and BAM! Right to left field, sending Talley and Banes home. Giving the Lions a 5-2 lead." 

At some point during the retelling, you became lost in the memory of the last time you saw him this excited over something. It was a few months ago. He had just rewatched The Holy Trilogy*, for the millionth time and as always, he insisted on reenacting his favorite parts for you, complete with choreography, and sound effects. Handsome as sin and goofy as hell, it was a lethal combination.

When you failed to react accordingly to his crowning achievement, he paused, turning sheepish, "We, uh, we won. I did a thing. It was cool."

“Yay. Good job,” you clapped, watching his much too handsome face in awe. 

“It's okay. You don't gotta pretend...," he said, as he looked down, kicking the earth with the toe of his sneaker, "It was a good game, though. The comeback alone..." 

"Stop. Baseball's not my thing. It's like, how you get all fanboy over that grandpa music you listen to or after you fix something on that old ass car of yours. Just because it's not something I'm into doesn't mean I can't be excited for you."

"Classic," he cut in, his voice held a clear warning to watch what you said about _her_ , "Baby is never old." 

"Yeah, yeah, she's classic," you rolled your eyes, but underneath your faux disdain, a smile was blooming, "But seriously, I like that you don't pretend you're too cool to, like, still be into things, that there's more to you than those idiot friends of yours or whoever you're hooking up with this week. Speaking of, why aren't you out with Cassie tonight?" 

"She went shopping or something. I dunno. I don't get it. How many pairs of shoes does she need? She can only wear one at a time," he shrugged before motioning to the street with his chin, "Gonna tell me what that was all about? You know, since it got me injured, and all.”

"Shut up. Your hand is fine.”

With a straight face, he said, "Pretty sure I need to go to the E.R. They'll _probably_ have to amputate. Your little screaming match with dickcheese just cost me a future in the Major League. I. Hope. You're. Happy." 

"Oh, for fucks sake, Dean. We broke up, okay," you said, cringing, as you waited for his response. 

“Fuckin' finally," Dean said, much louder than necessary. 

From somewhere inside 53 Barker Avenue, his father shouted from a window, "Dean! Keep it down!" 

Once you reigned in the giggles over his father's admonishment, you said, "Gee, Dean, tell me how you really feel." 

He lowered his voice lower and said, "Seriously, Y/N, what were you doing with him? He's a... he's such a... I mean, come on."

"A dick?"

"Yes," he said, breathing a sigh of relief that you said it first, "He's a monumental dick. Plus his hair sucks and he drives a freakin' Suzuki. You deserve better than that."

As the corners of your mouth crept up into a smile, you agreed with a nod, "You're right. I do. I definitely deserve someone with a much better car." 

"Damn straight!" 

And John Winchester was back, shouting from the window again, "God damn it, Dean. Keep it down." 

Your eyes widened as you stifled a giggle at the scolding, and he returned your look with a contrite little shrug. Silence took over the banter and the two of you began to fidget. You played with your hair as Dean looked around the street before finally speaking up. "So... uh... are you?" 

"Are I... what? Use your words, Dee."

"Uhh," he stammered adorably. Whatever was on his mind, was either very big or very personal, but by the way he wasn't looking directly at you, you were guessing it was the latter, "What he, uh, Cole, you know, what he said before."

You thought hard before it came to you. Laughing, you playfully shoved his shoulder and said, "Are you asking if I'm frigid?" 

"Maybe," he mumbled, looking to the ground, before his eyebrows raised expectantly for you for the answer. 

You shook your head, unable to believe the words you were about to say, "No. God, no, just... he couldn't turn on a light switch."

"Really? That's... well, that's just... that's unfortunate," he started off sounding sincere, but there was a definite smirk peaking out from beneath the words.

Then you noticed something odd in the way Dean was looking at you, with soft, contemplative eyes and suddenly, the air grew cumbersome, making your mouth dry and your palms sweat. Taking a backwards step, you used the space to gather your senses and discreetly wipe your hands on the back of your jeans.

"I should probably...," you turned your head, giving your house a quick glance before turning back to the weight of his stare, "Bossy's waiting up." 

With a little wave, you started across the lawn, but before you got too far, he called out, stopping you. He jogged the few feet to catch up to you, and you spun around to face him, but he was standing just a little too close, "Can I ask you something?" 

Pushing the hair out of your face, you nodded. 

Dean's tongue slightly poked out of the corner of his mouth before it swept over his bottom lip, making it glisten and your cheeks started to burn as your thoughts went to places it had no business going. 

Rubbing at the back of his neck, he raised his eyes to yours and said, “When was the last time you were really kissed? A good kiss. One that made you... I dunno... feel special. And don't say dickstain cuz I'll know you're lying." 

The longer it took to come up with answer, the more embarrassed you became and having Dean's eyes on you was not helping, but after a few silent minutes, you found the answer you were searching for.

"Got it! That exchange student, Mick something... Mick Davies! Last year, we skipped a pep rally or something and messed around behind the tennis courts. Accents are totally hot. Huge turn on," and you could've stopped talking but nervous energy kept your mouth moving, "Is that a fetish? Do I have a fetish? People with fetishes are really weird. Does that mean I'm weird?" 

"A year, huh? That's much too long to go without a good kiss," Dean's forest green eyes roamed your face before landing on your mouth. Taking your hand, he gently pulled you closer to his well defined chest, "Something should probably be done about that." 

And stop. 

_Wha- What the hell was happening?_

All logical thought started slipping from your brain, like how what he was proposing was so very wrong, and, how, only moments ago, you broke up with your boyfriend. Not too mention Dean was dating someone, who happened to be a kinda, sorta friend of yours, but the biggest thing that you should have been thinking about was that you really didn't want to turn an impulsive moment into an epic regret. 

But as his perfect, pink lips moved closer toward yours, you didn't think about any of those things. Instead, when his lips made contact with their target, and tiny kisses were placed upon your lips, all you could do was part them. And how eagerly they parted to welcome the velvety caress of his tongue against yours. 

Into unfamiliar caverns, curious tongues ventured to explore, flirt, and tease. The kiss started off slow, all minty and soft, needy and warm, but soon you were urging him on. You gripped the back of his neck, and taking the hint he deepened the kiss, smashing his lips to yours. There was confidence in his every movement, yet, his fingers were hesitant as they toyed with the hem of your shirt before slipping beneath the hem, gripping and stroking your skin. 

It was with regret that you untangled your tongue from his, breaking the kiss. Shy eyes avoided the intensity of Dean's as you ran a thumb over your swollen lips where a hint of a smile had formed. "Let's, uh, yeah. We should definitely do that again." 

With a devil's grin, Dean's hands tugged you back to him, closing the small gap that was between you. 

"I didn't mean... hmph." 

The return of his mouth on yours put a stop the words, lighting you up all over again. It was harder to end the kiss the second time around, either because his hands were holding you in place or maybe it was because the second kiss was even better than the first.

Tearing yourself away, he held onto your hand, refusing to let you go, turning the intense moment playful. When you finally freed yourself and said goodnight, he watched you walk to the stairs. He was still watching as you bounced, giddily, up the steps but even after you opened the door, you took a peek to find he hadn't moved an inch. 

"What are you doing?"

"Making sure you get home all right." 

You laughed as you stepped inside, calling out behind you, "You are such a dork." 

"But I'm the best dork," he shouted back as the door closed behind you. 

Ignoring your sister, who was shouting your name, you took off up the staircase. You hopped on your bed and pulled up the window blinds. It was as much of a surprise as it wasn't to find Dean, sitting on his bed, waiting in the window, just like he'd done back when you were kids.

That night, you fell asleep with a smile that refused to leave your face. You'd worry about the consequences tomorrow, and whatever they might bring. 

**Notes for the Chapter:**

> Hope you enjoyed this. The next chapter should be up soon.
> 
> *if you know anything about baseball you've noticed that i don't, so if it doesn't make any sense...i apologize.
> 
> **"the holy trilogy" was used in the movie, Chasing Amy in reference to the original Star Wars movies.


	3. A Case of the Ex

**Notes for the Chapter:**

> There's no need to reminisce 'bout the past  
> Obviously 'cause that shit did not last  
> I know how a woman will try to game you  
> Don't get caught up because baby you'll lose.
> 
> [Mya - A Case of the Ex](https://www.youtube.com/watch?v=0sq14JocSAs)

2008

After checking his watch, again, Dean signaled the bartender for another beer. Benny had just taken off, and there was at least another hour to kill before Y/N got home from her class, maybe more if she went out after and he wasn't in the mood to go home to an empty apartment. He didn't like when she was out with her grad school friends. He didn’t know them, didn’t care to know them, and certainly didn’t fit in with them.

It's not that he was some controlling dick that didn’t want her to have a life outside of him, but he liked it better when she'd go out with Charlie or Meg, or any friend of hers he trusted, had known for years. 

Sighing, Dean reached for the full bottle just as the bartender was taking the empty away. He took a long pull and stretched his neck from side to side, trying to loosen the days tension from his neck. It had been a long day, and he wanted to put it behind him. Everything in his life seemed to be changing without his consent, and he wasn’t loving it.

If he went home when Benny did, he’d be sitting on the couch, annoyed, alone and thinking too much about the new life she was making that he wasn’t a part of. That new life came with jokes and stories he didn’t understand, knowledge he didn’t need, and people he didn’t care for. It was also starting to make him nervous. What if, at some point, she realizes that she could do so much better than a mechanic working in his father’s garage? She had to know that she could do better, right?

His insecurities reached a new low the other night when he overheard her talking with Y/Mother’s/N about going for her doctorate. She wasn’t even done with grad school, but there she was in their kitchen, low talking about more fucking school.

What about his -wait. scratch that- what about their plans? Of course, he meant "their". Those plans weren't just his. Though they hadn’t actually talked about the future in some time, still those plans were all worked out in his head. He knew how he’d ask her, that was the easy part, and he already found the ring, saw it when he passed by a jewelry store on his lunch break. He'd even taken Sam to see it the last time he was home from college, and just to be really sure it was The One, he asked Meg to meet him one afternoon to get her opinion. 

But with how everything was going, popping the question felt less like the sure thing than it had only months before. After watching her come and go with her new friends from study group, and then to learn, for the first time in years, he was being left out of decision about her future, how was he to be sure she’d even say yes. Especially when there were guys out there that didn't leave their clothes on the floor, or day drink just because they could. Ones that didn't come home covered in motor oil or track it all over the house because they forgot to take off their boots when they got home. Guys who were smarter and owned more than one suit. Guys who actually wanted to spend a Sunday at the farmers market instead of inviting their friends over to watch the game. How did she not see that she deserved more than a college dropout that was still hanging around with the same guys he hung around with in High School? 

What if she did? What if she had? What if she wasn't happy coming home every day to a mechanic in their shitty walk up, even though she was partly responsible for who he'd become? After the accident, when the doctors told him he was done playing ball, it was Y/N who brought up how he’d be much happier working for his dad than staying in school. Hell, she even went with him to break the news to his parents, not that his decision completely surprised them.

Maybe he waited too long? Once he half-ass asked her to marry him, during their freshman year of college, and her reaction was less than awesome, but he understood her reasons. If only she hadn’t told him to ‘get the fuck outta here with that marriage shit’ back then, he wouldn’t feel like he didn’t belong in her world now. They would’ve been several years into a little world of their own, one with kids and a house, and summer BBQ’s in the back yard with their friends. Where Uncle Bobby would endlessly tease y/n about naming the next kid after him and his dad, with his dog like hearing, would probably interrupt, and say something like, ‘if it's not named after me… it sure as hell ain’t being named after you’. Instead, that imaginary life he built for them was feeling farther away than ever before. 

He sighed, checking his phone before flagging down the bartender for another beer with a shot of Jack on the side, hoping something a little stronger would force all the ‘what if’s’ back into hiding.

The sweet burn of whiskey was still travelling down his throat when from behind him he heard a voice straight out of his High School yearbook. 

“Oh my God. I don’t believe it. Dean Winchester sitting all by his lonesome on a Thursday night. What are the odds?”

He spun the bar stool around, coming face to face with one of his high school conquests. “Lisa,” he breathed out, sounding half surprised, as he ran a hand up the back of his hair, “Shit, how long’s it been?”

Placing a hand on his arm, she leaned into him and flashed a smile, “God, probably not since graduation.”

“Yeah, that sounds about right,” he nodded, remembering the night they graduated, when a very drunk Y/N gave the woman standing before him one hell of a shiner right before hurling all over his mother's Hydrangeas. Man, if she were here now, she’d have lost her mind, may have even reenacted that night, just for the audacity. Though, if Y/N was there with him he was fairly certain Lisa never would have gotten this close.

“So, uh, you back to Lawrence?”

She laughed, "Oh no. I'm just here til Sunday. My parents, they keep trying to talk me into moving back but I don’t know...”

“Oh yeah? Huh,” he said, raising the bottle to his lips, and tipped it back.

Leaning on the empty stool next to him, she looked around curiously, “Are you here by yourself?”

He tilted the neck of his bottle toward the door, “Just missed Benny. He has an early meeting or something.”

“Oh. Damn. It would’ve been nice to see him. Is he still cooking at that restaurant? What was it called,” she laughed, “Shit. Why can’t I remember the name of that place?”

“It’s hard to keep track with him. Either he’s leaving one place for something better or getting fired and going back to the place he just quit.”

With a bemused, nostalgic grin, she shook her head, “Some people never change, huh? What about you? Still at the garage?”

“That I am, that I am,” he nodded, taking another long pull from his beer when he noticed a table of women trying to get Lisa’s attention. He pointed toward them, “Think your friends want you.”

She turned and waved to the table before turning back, “Why don’t you come have a drink with us?”

“I… uh,” he pulled out his phone again, and looked down at the screen to see he had one missed call and one voicemail.

Lisa tugged on the sleeve of his flannel. "Oh come on. It'll be fun."

“I uh need...” slipping off the stool, he held up his phone and started to walk away when the level of his drunkenness hit him like _whoa_ , and he needed a second to pull himself together. Taking a few steps away from the bar, he listened to the message and it was exactly what he thought it would be.

>   
>  _Babe, I’m going to grab a coffee with Jennifer, you know, the one you keep insisting played the little girl in Curly Sue. ::she gave a breezy, little giggle:: I swear, you are the only one who even remembers that movie. Anyway, I won’t be late. Oh. Hey. If you get this soon, let me know if you want me to bring home anything. Hope you’re having fun and tell Benny I said hi. Oh yeah and ditto._

He looked down at the screen and shook his head, in what was either disbelief or amusement, though it was more likely a mix of the two. A grin spread across his lips. He couldn’t believe her sometimes. She fucking Swayzed* him. Even if it was from _Ghost_ , he’d let it count for now, but next time she'd really need to up her game. 

He scrolled to Y/n's number, finger hovering to return the call. He thought about heading home, and what he'd come up with to Swayze her back, but when he looked over to the bar, he saw Lisa, waiting with a smile. Considering all he had to drink it probably wasn't the best idea to drive home just yet. He shoved the phone back in his pocket and returned to his stool.

Lisa pursed her lips, and lay on the concerned eyes a little too heavy, “Something wrong, Dean?” 

“Yeah, uh, no. I can stick around for a little while."

With that, Lisa took him by the arm and led him over to her friends table. No more drinks turned into two, than three and before he knew it the only other person left at the table was Lisa, who had turned a little too touchy while reminiscing as she attempted to rekindle an old spark. 

"Why did we ever break up?"

"Damned if I remember." Dean looked around at the near empty bar before checking his watch. It was getting close to last call and he signaled for the waitress, "Time to switch to water."

Lisa frowned, playfully, "Now, where's the fun in that?"

"Still have to drive home."

"Yeah, I guess I should call a cab since my friends have all abandoned me."

Now, if he thought about the words that were about to come out of his mouth, he never would have said them, but he was still mostly drunk and he didn't so he did.

"I can take you back to your parents."

"Yeah? No. I don't want to inconvenience you. You have to be at work in a few hours. I can take a cab."

"It's not a problem."

  
  
  
  
_Shit! Shit! Son of a..._

In a strange house, in a strange room, he found himself in a strange bed, post sex, with someone he hadn't thought of since he was in High School. It was sloppy and selfish and it was over, and as he was trying to figure out how long he needed to lay there, he was slowly realizing the magnitude of what had just happened. Now that he was sober enough to flee the scene he counted to ten before he rolled out of bed, and searched the floor of the dark room for his clothes.

From the bed, Lisa called out to him, urging him to stay the night, but he was already half dressed and half out the door. He needed to get home, needed to take a million showers, so he would no longer smelled like her and his deception.

When he was on the road, his guilty brain started to work double time on the cover up. He needed a good story in case Y/N was awake when he got home. Scrolling to Benny’s number, he chewed on his lip as he pressed call. Benny would help him out. Benny had been helping him since the eighth grade.

On the fifth ring, Benny finally picked up, sounding really tired and really pissed.

“Whoever this is, you better be lyin' in the fuckin’ morgue cos there ain’t no other reason to be callin’ at this hour.”

“Yo, Benny, it’s Dean. I need a favor.”

“Everything okay, brother?”

“Look, if anyone and I mean anyone, and by anyone, I mean Y/N, asks what we did tonight, you never went home early. We closed down the bar like old times, okay?”

“Yeah, sure, whatever you need, but tomorrow you’re gonna tell me how big you fucked up and why you want me lyin’ to Y/N.”

“Thanks, man. I owe you one. Get some sleep.”

“Dean, wait.”

“Yeah?”

“Whatever you did after I left, and I'm not judging here, but there’s only one way this ends. Either you tell Y/N what you did and hope she forgives you or she figures it out and trust me, they always figure it out and if it doesn't come from you I guarantee there won't be any chance of forgiveness.”

  
  
  
  


Still feeling the end effects of the booze, he, sluggishly, climbed the stairs to the apartment, and fumbled with his keys, taking four tries before he found the right one then another three tries to get it in the lock. 

Walking through the dark apartment, he stopped at the bedroom door, poking his head in, only to find Y/N fast asleep. Of course she was asleep. She needed to be up for work soon. Carefully, he closed the door and jumped into the shower. 

Half a bottle of body wash later, he finally slipped into bed. She stirred, barely opening her eyes, and mumbled. "'m up, 'm up. Just shut mmm eyes.” 

"Go back to sleep, babe. You don't need to get up yet."

"Mmm, okay." Sleepy limbs slowly re-positioned themselves as little sounds of frustration left her lips, and didn't stop until she had made it into her default sleeping position: head on his chest, an arm wrapped around his body, "Smell good."

His right hand combed through her Y/HC/H hair, before slowly sliding down to rub her back. It didn't take long for her to fall back to sleep.

Benny was wrong. He could do this. He could pretend nothing happened. It wouldn't even be lying. Not really. The odds of her asking something as specific as "Did you run into Lisa and fuck her", were slim at best. As long as he never did anything like that again, everything would be just fine.

**Notes for the Chapter:**

> *I don't recall if they used the term Swayzed on SPN or if it was on another show. How I Met Your Mother, maybe? Anyone know?


	4. Tonight, Tonight part 02

**Notes for the Chapter:**

> Time is never time at all  
> You can never ever leave, without leaving a piece of youth  
> And our lives are forever changed  
> We will never be the same.
> 
> [Smashing Pumpkins - Tonight, Tonight](https://www.youtube.com/watch?v=NOG3eus4ZSo)  
> 

Back in 1996 

After Y/N disappeared inside, Dean took off across the lawn, into his house, up the stairs and straight to his room. He pulled up the window shade and waited. It was stupid, and she probably wouldn't even show up, but if she did then maybe he had a shot.

Just to be clear, he hadn't been sitting around moping like some puppy left at home for the last five months and seventeen days, waiting and hoping she'd break up with that ass stain. Nope. That would be pretty ridiculous if he did, right? Dean Winchester was no piner, and he certainly didn't need to wait for anyone, not when there'd been plenty of girls letting him round the bases with minimal effort. Not to mention he'd been seeing Cassie longer than Y/N had been with Cole. 

Up until four months and three days ago, the very idea of doing anything not platonic with Y/N felt about as wrong as wanting to kiss his brother. Just thinking about her like he thought about others girls felt dirty, and not a good dirty, but after seeing her with Cole, acting like a couple that first time, he realized something. 

He realized that Y/N wasn't just any girl. She was his oldest friend, and his partner in crime. The first time he disobeyed his parents was because of her. It was summer, something like twelve years ago, and she wanted an ice cream cone. So with pockets stuffed with stolen change, and promises to their parents of only walking around the block, they headed off on their first adventure to the Dairy Queen and because he was the oldest (by several months), he made sure to hold her hand whenever they needed to cross the street. Did Cole even know that she preferred chocolate soft serve ice cream to vanilla, and cherry dip over sprinkles? 

They shared other firsts, as well. Their first drink was from whatever bottles were the fullest in his parent's liquor cabinet, one afternoon while his mom was out shopping. They'd even thrown up together. Her making it all the way to the kitchen sink, while he did the deed right on the dizzy yellow linoleum. 

She was also the first girl to show him _hers_ , after one of her birthday parties, the one with the clown that scared the crap out of Sammy. All the guests had gone home, but they stayed outside playing on her swing set when things took a turn, but when it was time for him to pay up and show _his_ , he ran home, leaving her standing behind her father's shed, never honoring his end of the deal. That earned him one hell of a punch the next time she got him alone.

Okay, maybe he had been harboring a few feelings for her over the years, and all those feelings he buried were the reason he went through her friends like Kleenex. Except there was a flaw in his whole "Notice Me" campaign - He really, really, really did like Cassie. She was pretty and smart. She got along with his friends and her parents worked late _a lot_. Still, no matter how much he liked his girlfriend, it didn't stop him from kissing Y/N, _twice_ , and because those were some serious kisses, he would've gone for a third if it just took her a little longer to go inside

It was then her bedroom light turn on. She waved at him before the room went dark again, and he headed to the kitchen to get some ice for his hand, a smile fixed upon his face. She had remembered.

After wrapping some ice in a towel, Dean went to find Sammy to see what he watching before turning in.

"What happened to you hand," Sam asked, with a curious tilt to his head as he lay on the couch, munching on some popcorn he made earlier.

“Nothing. Shut up. Why aren’t you in bed,” Dean said, throwing an irritated look at his brother for taking up the entire couch before he took a seat on the floor to be closer to the coffee table, and the bowl of popcorn, “What are we watching, Sammy? SNL or Mystery Science Theater?”

Grimacing at the nickname, he said,“MST3k. Duh.” 

With his good hand, Dean shoved a handful of popcorn into his mouth, nodding his approval.“Cool.”

“What happened outside… with Y/N," Sam said, as he continued to stare at his brother.

Dean turned his head, giving his little brother his full attention, “She was having some trouble with that guy so I played superhero... Well, sort of. She kinda bit him before I could do anything. But I still got to hit him.”

“How much damage could a bite really do?”

“Here. Check this out,” Arranging himself on the floor, Dean pushed the sleeve of his bootleg Led Zeppelin tee, over his shoulder, revealing a scar that was now a faint impression of teeth on his upper arm, and Sammy leaned over for a closer look, “We were ten. That shit’s permanent. She broke the skin and everything. Never fight a girl, Sammy, they’re always breakin’ the rules, especially Y/N, she plays dirty.”

With half a laugh, and a shake of his head, he pushed the sleeve back down and continued,“Kind of deserved it, though. Another thing about girls, never tease them about their stupid music, no matter how shitty is. Next time you see Y/N, ask her who her favorite New Kid is."

When the show first cut to commercials, Dean pushed himself off the floor and headed to the kitchen when Sam called to him. Dean turned back around, "You want something to drink?" 

“Yeah, sure, but…,” Sam stopped, and tried to organize his thoughts. He thought he knew the answer, thought he saw his brother kissing Y/N when he looked out the window but maybe he didn't see anything. 

Dean threw his head back and huffed, impatiently, "Come on, dude. Commercial break."

But Sam didn't finish his inquiry and Dean continued into the kitchen, quickly, returning with a couple of juice boxes, ready to watch a terrible movie. He tossed a drink at Sam, who was in deep thought.

He sat back down on the carpet."Whatcha thinking over there, Sammy?"

Sam shook his head, "Uh, I'm supposed to tell you that Cassie called before, while you were outside not being a superhero. Mom was a little, you know, with her, cause it was late.”

Dean shrugged, settling back down on the floor, and turned his eyes back to the TV. Maybe he wouldn't have to return that call, and maybe he wouldn't need to play mediator with Cassie and his mom, again, because he was one hundred percent positive it has been different kissing Y/N, and there was no way in hell she didn't feel it too.


	5. Putting the Damage On

**Notes for the Chapter:**

> So now I'm wishing  
> For my best impression  
> Of my best Angie Dickinson*  
> But now I've got to worry  
> Cause boy you still look pretty  
> To me. 
> 
> [ Tori Amos - Putting the Damage On](https://www.youtube.com/watch?v=SZ2mvMBcXjE)

As with most things she did, when Meg walked past you into your parent's house, she acted like she owned the place. Tossing her jacket and bag on the love seat, she stood with her arms crossed, eyeing the junk food that cluttered the coffee table as you stumble back to your well lived in spot on the couch, the blanket hanging off your shoulders dragging limply along the hardwood floor.

“Don’t mean to interrupt ‘the 8 year old left home alone for the weekend' party you got going on here, mopey, but we need to get going." 

You blinked with zero understanding. "Where..." 

"Uh. The dress fitting. _You_ made the appointments.”

Shit. You ran your hand through your messy hair and tried to look apologetic. As with everything that didn't have to do with your breakup, you completely forgotten about this. The appointment was made long before the _incident_. 

“That was today?" 

"That was today," she repeated back to you, the words sharp and clipped. She was irritated, though it was still hovering in the calmer stages, but you worried that what you had to say next would send her into a murderous rage. 

You took a breath, readying yourself for the disappointed Meg look you've dreaded most of your life. “Look, Meg, with everything that's…”

Not giving you the chance to finish, Meg cut you off, and said, “No. Fuck no. You’re not doing that to me.”

“I didn’t…”

“No, but I _know_ you, and no.”

“Meeeeeeeeeeeg,” you pleaded with your friend, “Come on. You know…”

“Oh, I fucking know everything. I know this is a really bad time for you, but you will not go back on your word. You will be my Maid of Honor and you will suck it up. So start practicing your internal screams, death glares and your pretty plastic smile or whatever you need to get you through this cos I am not walking down that aisle without you," her brown eyes bore into your sad, frustrated face, "Besides, who else is going to stop me from slaughtering Cas’ entire family when one of them makes a comment about something I do or don't do.”

“Oh come on. They aren’t all bad.”

“They think I’m the spawn of Satan.”

You shrugged slightly. Maybe that was a fair assessment when the whole Cas/Meg thing first began but as the years went on it became much less accurate. You thought about Cas' family and suddenly one of his brothers came to mind, and you hoped it would perk up her mood. 

“Gabe doesn’t think you’re…”

Meg grimaced at you. “Oh right. The black sheep, fuck up brother who wants nothing to do with _that_ family, doesn’t think I’m Cas' ruination. That makes everything all better.”

“Why does it matter now what Cas’ family thinks? He's been in love with you since…,” you paused trying to remember the first time you noticed Cas was smitten with your friend but could not pinpoint a time when he wasn't, “I don’t even know how long and he’s never once cared about about your satanic parentage.”

“Funny. Like you wouldn’t be freaking out if Dean's entire family thought you weren’t good enough for their perfect little boy. Oh wait, John and Mary have always known what a colossal fuck up their son can be," Meg was quick to apologize the second she noticed the slight wince you made, "Seriously, though. Want me to make Cas find a new best man? Cos I’ll do it. There is no way I'm letting _him_ ruin _my_ day.”

She would, too. The offer was sincere and oh so tempting, but you could never ask that of the couple. There was too much history there. Dean meant just as much to Cas as you did to Meg. 

“No. God no, Don't do that. I mean, how would you feel if Cas told you to find a new maid of honor?”

“Like he’d ever,” she chuckled. The thought of Cas trying to make Meg do anything was hilarious. Quickly she turned serious, "Look, I know it all feels end of the world terrible right now, but it won't always suck this bad. There was a time when you were fine without him.”

“Yeah, like what? Ten years ago. Do you have any idea how long that is in relationship years?”

“It really is your own fault," she teased. "You shoulda walked back in High School. Hell, that one time, you kinda did. You just gotta be that 'I don't need him or his shit' girl again.” 

"Really? _Really_ , Meg? Is someone forgetting the role she played in all of this?" 

"I don't know what you're talking about," she dead up lied with a straight face before a small, knowing grin started to show. "Now, come on, get your ass up off that couch." 

Back in 1996

On any other Sunday morning, if you were awoken by _Tom Sawyer_ blasting outside your window, you’d have stuck your head out the window, and screamed for Dean to turn that shit down, but on that particular morning you found yourself so unbothered by the noise that you were actually smiling as you rolled out of bed. Was your smile left over from the night before?

_Shit!_

_Last night._

_Oh no, no, no._

As the events from the night before came flooding back to you, your body slowly started the freak out process. Skin burning feverishly in shame while your stomach became a roller coaster, and not just the kind that went up and down, this was the the kind that tilted and did big loops, twisting and turning you upside down until you were ready to hurl. 

Those lips, so soft upon your own, and those eyes, even under the night sky, were brimming with... 

_Nope. Stop that right now._ _Karma is totally going to drop a house on your ass after what you did._

Whatever you thought you felt, no matter what you thought you was there, those kisses never should have happened. You should have been smart enough to stop him, thrown up a hand, and blocked his lips from reaching yours or you could have dodged him using Axl's serpentine move. 

Only you didn't stop him. Not the first time or the second and if there had been a third, you doubted you'd have tried to stop that one either. You let yourself get lost in a moment and you suddenly wondered if he bothered to give those kisses a second thought or maybe you were worried that he hadn't? Did you want him to? Did you want them to mean more? He's never thought of you in _that_ way before. Why would that change now? 

Maybe this was all your fault? Did you let him kiss you because you just broke up with Cole? Nah. The Cole thing had run it's course and you weren't feeling any kind of way about that, if you were being honest. What if those kisses happened because Dean thought you were sad and he was trying to make you feel better? 

You dressed quickly, and headed next door to clear up a few things.

There was a slight chill in the air and you crouched down next to the Impala to wait for Dean. When you decided he was taking too long, you turned the dial on the little radio off, knowing it was the quickest way to get his attention.

Instantly, a shout came from beneath. “Hey!”

“It's way too early for Rush, Dee.”

Rolling out from under the car, you noticed a grin has already broken out upon his face. Sitting up he reached for a rag to wipe his hands clean and said, “Hey. I was going to call you when I was done.” 

He spun around on the mechanic's creeper to face you, rolling it until he was sitting between your crouching legs. Suddenly he was a breath away with a smile that lit his eyes up, bright and wide. He licked his lips, and said, "Hi."

Your heart fluttered and you couldn't recall someone ever smiling at you like that before, but it was a smile you could definitely get used to. He pressed his hand to your cheek, before letting a finger trace a line down your face, and over your bottom lip. Before you could say a word, his mouth was on yours, and you relented, getting lost in him once again. 

_Oops._

You couldn't help it. You couldn't stop it. No sane person would dare refuse such an enticing offer.

He pulled away from your swollen lips with a grin, and said, “So, you, uh, wanna catch a movie later or something?”

You pressed a hand to his chest, keeping him at a distance, keeping him from kissing you again. “But you're still with Cassie.”

He groaned, taking your hand from his chest, letting his fingers tangle with yours. "Yeah, but I was thinking that we could have something really good on the side**." 

And that was when the world came screeching to a halt. 

When those words exited his mouth, filling the minuscule space that lay between the two of you, you snatched your hand back unable to believe what he said, what he was asking of you. Asking so easily, like it was little more than borrowing a pen or to copy your homework and you couldn’t decide what angered you more - that he actually thought you’d agree to the arrangement or that he dared to fucking ask that of you in the first place. 

Though your heart ached, incredulous laughter flowed from your chest, all jagged and sharp. You stood from the pavement, looking down at him with disappointed eyes and shook your head, sadly. "Yeah. No." 

Crossing the property line, you never looked back.

**Notes for the Chapter:**

> *Actress on the show Police Woman (1970's) that never took any shit from anyone.
> 
> **This actually happened to me, sans the cool car and the cool music, and obviously the guy wasn't nearly as cool.


End file.
